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Potential histidine decarboxylase inhibitors. II. 3-(4-Imidazolyl)-2-pyridine and piperidinecarboxylates
Authors:J I Degraw  J S Engstrom  M Ellis  H L Johnson
Abstract:The synthesis of methyl 3-(4-imidazolyl)-2-pyridine ( 12 ) and piperidineearboxylates ( 13 ) is described. Hydrolysates of these esters were found to be devoid of inhibitory activity against histidine decarboxylase. 3-Bromoacetyl-2-pieoline ( 2 ) could be converted to 3-(4-imidazolyl)-2-picoline ( 6 ) by two different routes. Treatment of 6 with peroxide and acetic anhydride, followed by transesterification yielded the 2-hydroxymcthyl pyridine ( 9 ). Oxidation of 9 followed by esterification gave the imidazole pyridine acid ester ( 12 ) which after hydrogenation afforded the imidazolylpiperidine ester ( 13 ).
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